Hydrochloric Acid → 2,3-Dihydrobenzo(b)furan-5-carboxylic acid

HRID 2181644Notes

Reaction equation

HRID 2181644 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:12])C)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl[O-].[Na+].S(=O)(O)[O-:17].[Na+].Cl>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:17])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanoneHCID 23665760Sodium HypochloriteHCID 23665763Sodium Bisulfite

Product 1

HCID 6765832,3-Dihydrobenzo(b)furan-5-carboxylic acidYield 97%

Procedure

A mixture of 1-(2,3-dihydrobenzofuran-5-yl)ethanone (4.0 g, 25 mmol) and sodium hypochlorite [160 mL of a 6.0% aqueous solution, (Clorox brand of bleach)] at 55° C. is stirred for 1 h. The mixture (now homogeneous) is cooled to rt and solid sodium bisulfite is added until a clear color persists. Hydrochloric acid (80 mL of a 1.0 N aqueous solution) is added, followed by extraction with EtOAc. The organic layer is washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 3.93 g (97%) of 2,3-dihydrobenzofuran-5-carboxylic acid as a white solid. 1H NMR (400 MHz, CDCl3) δ 11.0-10.3, 8.00, 6.87, 4.72, 3.31.

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer is washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d68a09877a1545c29a21e20bdb051000
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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